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Extraction and Analysis of Phenolic Compounds in Rice: a Review

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Extraction and Analysis of Phenolic Compounds in Rice: a Review molecules Review Extraction and Analysis of Phenolic Compounds in Rice: A Review Marco Ciulu 1,*, Maria de la Luz Cádiz-Gurrea 2,3 and Antonio Segura-Carretero 2,3 1 Department of Animal Sciences, Division of Quality of Animal Products, University of Göttingen, Albrecht-Thaer-Weg 3, 37075 Göttingen, Germany 2 Department of Analytical Chemistry, University of Granada, c/Fuentenueva s/n, 18071 Granada, Spain; [email protected] (M.d.l.L.C.-G.); [email protected] (A.S.-C.) 3 Research and Development of Functional Food Centre (CIDAF), PTS Granada, Avda. Del Conocimiento 37, Edificio BioRegion, 18016 Granada, Spain * Correspondence: [email protected]; Tel.: +49-0551-3926085 Received: 16 October 2018; Accepted: 5 November 2018; Published: 6 November 2018 Abstract: Rice represents the main source of calorie intake in many world countries and about 60% of the world population include rice in their staple diet. Whole grain rice, also called brown rice, represent the unpolished version of the more common white rice including bran, germ, and endosperm. Many health-promoting properties have been associated to the consumption of whole grain rice and, for this reason, great attention has been paid by the scientific community towards the identification and the quantification of bioactive compounds in this food item. In this contribution, the last five years progresses in the quali-quantitative determination of phenolic compounds in rice have been highlighted. Special attention has been devoted to the most recent strategies for the extraction of the target compounds from rice along with the analytical approaches adopted for the separation, identification and quantification of phenolic acids, flavonoids, anthocyanins, and proanthocyanidins. More specifically, the main features of the “traditional” extraction methods (i.e., maceration, ultrasound-assisted extraction) have been described, as well as the more innovative protocols involving advanced extraction techniques, such as MAE (microwave-assisted extraction). The predominant role of HPLC in the definition of the phenolic profile has been examined also presenting the most recent results obtained by using mass spectrometry-based detection systems. In addition, the most common procedures aimed to the quantification of the total amount of the cited classes of phenolic compounds have been described together with the spectrophotometric protocols aimed to the evaluation of the antioxidant properties of rice phenolic extracts (i.e., FRAP, DPPH, ABTS and ORAC). Keywords: rice; phenolic compounds; phenolic acids; flavonoids; anthocyanins; proanthocyanidins; antioxidant activity; extraction; HPLC methods 1. Introduction Cereals play a meaningful role in the human diet not only for the wide variety of nutrients provided but also for their significative caloric contribution. Among cereals, rice is nowadays one of the most important from both a nutritional and an economic point of view since about 60% of the world’s population include rice in their basic diet. More specifically, rice is the most cultivated crop in the Asian-Pacific region and it constitutes the staple food in several developing countries such as India, Bangladesh, Vietnam, etc. [1]. Brown rice, also called whole grain rice, is the result of the removal of the inedible outer hull and, unlike the common white rice, it includes the germ, bran, and endosperm. Depending on the Molecules 2018, 23, 2890; doi:10.3390/molecules23112890 www.mdpi.com/journal/molecules Molecules 2018, 23, 2890 2 of 20 various pigmentations of the outer layer, whole grain rice can be classified as black, purple, red, etc. Several health-promoting and nutraceutical properties have been associated to the consumption of whole grain rice [2]. For instance, in the study conducted by Hallfrisch and co-workers (2003) a decrease of the cardiovascular risk was observed because of enhancement of the intake of whole grain foods in the daily diet [3]. Moreover, the consumption of pre-germinated brown rice as staple diet proved to produce a positive effect in the countering of depression, hostility and fatigue in a group of breast-feeding mothers [4]. In addition, the antidiabetic properties of germinated brown rice have been reviewed by Imam et al. (2012) [5]. Many of the documented health benefits of brown rice have been associated to the occurrence of polyphenols in its chemical composition. It appears clear that the presence of phenolics in rice represents an added value for this food item whose inclusion in the daily diet is relevant not only for its nutritional content, but also for the related health benefits. Most of phenolic compounds traceable in rice are present in insoluble bound forms and only colonic digestion is able to facilitate the release of these compounds from cell wall materials [6]. Instead, the other fractions include the free and soluble conjugate forms. Phenolic acids constitute an important class of the phenolic fraction of brown rice, including both hydroxybenzoic and hydroxycinnamic acids. Figure1 shows the structure of some common phenolic acids detected in rice. Additionally, flavonoids, whose structure is characterized by the presence of an x-phenyl-1,4-benzopyrone backbone (where x = 2, 3), are a noteworthy part of the diverse phenolic fraction of rice. As illustrated in Figure2, the most common flavonoids of rice belong to a wide variety of subfamilies such as flavonols, flavones, flavanols, flavanons, isoflavones, etc. Phytochemical studies on whole grain rice brought to light many interesting aspects related to the presence of anthocyanins. This peculiar subgroup of polyphenols is noteworthy not only for being water-soluble pigments who contribute to the colour of fruit and vegetables, but also for their several well-documented health-promoting properties [7]. In vitro experiments performed on human cells proved the ability of anthocyanin extracts from black rice to inhibit the motility of cancer cells of various types [8]. In addition, this type of extracts seems to reduce platelet hyperactivity, hypertriglyceridemia and body weight gain in male dyslipidemic rats [9]. As shown by Figure3, derivatives of cyanidin, peonidin, malvidin and pelargonidin have been traced in rice [2]. Finally, the phenolic profile of red rice is characterized by the presence of proanthocyanidins. These oligomeric polyphenols, which include in their structure mainly (+)-catechin and (−)-epicatechin monomeric units [2], proved to possess a considerable antioxidant activity [10]. On the basis of the above, it is evident that the analytical determination of the quali-quantitative profile of polyphenols is a necessary prerequisite not only to define the nutritional qualities of whole grain rice, but mostly to investigate on the health benefits associated to the consumption of this food item. The broad variety of structures of the target analytes and the usually low concentration levels (sometimes fractions of mg/100 g dry weight, [2]) imply the adoption of precise and accurate multistep analytical strategies able to correctly isolate, identify and quantify these bioactive compounds in a complex food matrix. In addition, in order to assess the reliability of the quantitative data a complete validation protocol is needed for the proposed procedures. Scientific literature offers several examples related to the quali-quantitative determination of polyphenols in whole grain rice along with the evaluation of the phenolic compounds-related properties (i.e., antioxidant activity). At best of our knowledge, no recently published review provides a comprehensive view on the state of the art regarding the analytical methods adopted for the definition of the phenolic profile of brown rice and the assessment of the bioactivity of the extracts. Hence, the primary goal of this contribution is to highlight the recent advances in this field focusing the attention on the studies carried out during the last five years. Special attention will be devoted to the extraction procedures aimed to the isolation of the target analytes, the chromatographic conditions adopted to properly outline the phenolic profile, the spectrophotometric protocols devoted to the quantification of the total content of specific classes of polyphenols and also to the determination of the antioxidant properties. Molecules 2018, 23, 2890 3 of 20 Molecules 2018, 23, x FOR PEER REVIEW 3 of 20 Figure 1. Hydroxybenzoic (a) and hydroxycinnamic acids (b) commonly found in rice. Figure 1. Hydroxybenzoic (a) and hydroxycinnamic acids (b) commonly found in rice. Molecules 2018, 23, 2890 4 of 20 Molecules 2018, 23, x FOR PEER REVIEW 4 of 20 Figure 2. Some flavonoids commonly found in rice. Figure 2. Some flavonoids commonly found in rice. Molecules 2018, 23, 2890 5 of 20 Molecules 2018, 23, x FOR PEER REVIEW 5 of 20 Figure 3. Some common anthocyanins detected in rice [2]. 2. Extraction and Clean-Up Figure 3. Some common anthocyanins detected in rice [2]. Extraction is a key step in the determination of phenolic compounds in rice. The main challenge is represented2. Extraction by and the necessityClean-Up to isolate compounds belonging to different classes (i.e., phenolic acids, flavonoids,Extraction proanthocyanidins is a key step etc.)in the and determination to remove possible of phenolic interferences. compounds Moreover, in rice. The the choicemain challenge of the mostis suitablerepresented extraction by the procedure necessity stronglyto isolate depends compound nots onlybelonging on the to type different of analytical classes information (i.e.,
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